NPASS Compound

Natural Product: NPC61004

Natural Product ID	NPC61004
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gly-Asp-Phe-Glu-Glu-Ile-Pro-Glu-Glu-Tyr-Leu-Gln
IUPAC Name	(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-carboxypropanoyl]amino]-3-phenylpropanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL411059
PubChem CID	16138839
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0003297] Organic Polymers [CHEMONTID:0003298] Polypeptides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 197199 0 0 0 0 0 0 0 0999 V2000 -6.3567 -17.3369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9668 -15.9666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5769 -14.5963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1870 -13.2260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2066 -13.9862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 -13.3761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6795 -11.8843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6227 -14.2578 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6227 -15.7578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1962 -16.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3145 -15.0078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1962 -13.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8971 -13.0442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8971 -11.5442 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4019 -10.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1519 -12.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9019 -13.3923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6519 -14.6913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9019 -15.9904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1519 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23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 23 29 1 0 29 30 2 3 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 36 39 1 0 31 40 1 0 40 41 2 3 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 44 46 1 0 42 47 1 0 47 48 2 3 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 2 3 52 54 1 0 49 55 1 0 55 56 2 0 55 57 1 0 47 58 1 0 40 59 1 0 29 60 1 0 21 61 1 0 13 62 1 0 5 63 1 0 63 64 2 3 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 68 69 2 0 68 70 1 0 65 71 1 0 71 72 2 3 72 73 1 0 73 74 1 0 74 75 1 0 75 76 1 0 76 77 2 0 76 78 1 0 73 79 1 0 79 80 2 3 80 81 1 0 81 82 1 0 82 83 1 0 83 84 2 0 84 85 1 0 85 86 2 0 86 87 1 0 87 88 2 0 81 89 1 0 89 90 2 3 90 91 1 0 91 92 1 0 92 93 1 0 93 94 2 0 93 95 1 0 91 96 1 0 96 97 2 3 97 98 1 0 98 99 1 0 97100 1 0 90101 1 0 80102 1 0 72103 1 0 64104 1 0 12 8 1 0 38 33 1 0 88 83 1 0 1105 1 0 1106 1 0 1107 1 0 2108 1 0 2109 1 0 3110 1 1 4111 1 0 4112 1 0 4113 1 0 5114 1 1 9115 1 0 9116 1 0 10117 1 0 10118 1 0 11119 1 0 11120 1 0 12121 1 1 15122 1 1 16123 1 0 16124 1 0 17125 1 0 17126 1 0 20127 1 0 23128 1 6 24129 1 0 24130 1 0 25131 1 0 25132 1 0 28133 1 0 31134 1 6 32135 1 0 32136 1 0 34137 1 0 35138 1 0 37139 1 0 38140 1 0 39141 1 0 42142 1 1 43143 1 0 43144 1 0 44145 1 0 45146 1 0 45147 1 0 45148 1 0 46149 1 0 46150 1 0 46151 1 0 49152 1 1 50153 1 0 50154 1 0 51155 1 0 51156 1 0 53157 1 0 54158 1 0 57159 1 0 58160 1 0 59161 1 0 60162 1 0 61163 1 0 62164 1 0 65165 1 6 66166 1 0 66167 1 0 67168 1 0 67169 1 0 70170 1 0 73171 1 1 74172 1 0 74173 1 0 75174 1 0 75175 1 0 78176 1 0 81177 1 6 82178 1 0 82179 1 0 84180 1 0 85181 1 0 86182 1 0 87183 1 0 88184 1 0 91185 1 1 92186 1 0 92187 1 0 95188 1 0 98189 1 0 98190 1 0 99191 1 0 99192 1 0 100193 1 0 101194 1 0 102195 1 0 103196 1 0 104197 1 0 M END

Standard InCHIKey	ZNEKMMIWGPUTGR-SQJOKQRMSA-N
Standard InCHI	InChI=1S/C66H93N13O25/c1-5-34(4)55(78-59(96)41(21-26-53(89)90)71-56(93)38(18-23-50(83)84)72-61(98)44(29-35-10-7-6-8-11-35)77-63(100)46(31-54(91)92)69-49(82)32-67)65(102)79-27-9-12-47(79)64(101)73-40(20-25-52(87)88)57(94)70-39(19-24-51(85)86)58(95)76-45(30-36-13-15-37(80)16-14-36)62(99)75-43(28-33(2)3)60(97)74-42(66(103)104)17-22-48(68)81/h6-8,10-11,13-16,33-34,38-47,55,80H,5,9,12,17-32,67H2,1-4H3,(H2,68,81)(H,69,82)(H,70,94)(H,71,93)(H,72,98)(H,73,101)(H,74,97)(H,75,99)(H,76,95)(H,77,100)(H,78,96)(H,83,84)(H,85,86)(H,87,88)(H,89,90)(H,91,92)(H,103,104)/t34-,38-,39-,40-,41-,42-,43-,44-,45-,46-,47-,55-/m0/s1
SMILES	CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=N[C@@H](CCC(=O)O)C(=N[C@@H](CCC(=O)O)C(=N[C@@H](Cc1ccc(cc1)O)C(=N[C@@H](CC(C)C)C(=N[C@@H](CCC(=N)O)C(=O)O)O)O)O)O)O)N=C([C@H](CCC(=O)O)N=C([C@H](CCC(=O)O)N=C([C@H](Cc1ccccc1)N=C([C@H](CC(=O)O)N=C(CN)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1467.64	Volume:	1423.861 ? Van der Waals volume.
Dense:	1.031	LogP:	-0.017 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.127 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.135 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	48.0	Rigid Bonds:	35.0
TPSA:	660.34 ? Topological Polar Surface Area.	H-Bond Acceptor:	38.0
H-Bond Donor:	21.0	Rings:	3.0
Heavy Atoms:	38.0

MedChem Properties

QED Drug-Likeness Score:	0.027	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.634	Fsp³:	0.545
MCE-18:	135.451 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.632	Fluc inhibitor:	0.182 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.06 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.937 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.006	Promiscuous compounds:	0.097

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.089	MDCK Permeability:	-5.221
Pgp-inhibitor:	0.0	Pgp-substrate:	0.085
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.232
Plasma Protein Binding (PPB):	55.476%	Volume Distribution (VD):	-0.644
Fu:	38.044% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

-0.494

Half-life (T1/2):

4.753

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.02	Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.785	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.596
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.863
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.001
BCF:	-0.314 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	2.531 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.851 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.502 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9518.1	Gardenia jasminoides var. grandiflora	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9518.1	Gardenia jasminoides var. grandiflora	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518.1	Gardenia jasminoides var. grandiflora	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	IC50	=	3700.0	nM	PMID[2002458]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC61004 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	21800
0.1-0.2	26516
0.2-0.3	1117
0.3-0.4	277
0.4-0.5	115
0.5-0.6	27
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.6542	Remote Similarity	NPC489828
0.6429	Remote Similarity	NPC489823
0.6226	Remote Similarity	NPC489827
0.5658	Remote Similarity	NPC484365
0.5634	Remote Similarity	NPC485114
0.5607	Remote Similarity	NPC5194
0.56	Remote Similarity	NPC485115
0.5577	Remote Similarity	NPC484363
0.5566	Remote Similarity	NPC489556
0.5563	Remote Similarity	NPC482981
0.5545	Remote Similarity	NPC241794
0.5419	Remote Similarity	NPC484964
0.5395	Remote Similarity	NPC484963
0.539	Remote Similarity	NPC485116
0.5315	Remote Similarity	NPC261934
0.5312	Remote Similarity	NPC484362
0.5299	Remote Similarity	NPC328649
0.5294	Remote Similarity	NPC486507
0.527	Remote Similarity	NPC485113
0.519	Remote Similarity	NPC489217
0.5188	Remote Similarity	NPC479140
0.5179	Remote Similarity	NPC489825
0.5096	Remote Similarity	NPC242482
0.5079	Remote Similarity	NPC326349
0.5079	Remote Similarity	NPC323336
0.5069	Remote Similarity	NPC482856
0.505	Remote Similarity	NPC200589
0.5047	Remote Similarity	NPC479068
0.5044	Remote Similarity	NPC489826
0.5031	Remote Similarity	NPC479141

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC61004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2845
0.1-0.2	5898
0.2-0.3	368
0.3-0.4	38
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data